2-(5-Amino-2H-tetra-zol-2-yl)acetic acid.

In the title mol-ecule, C(3)H(5)N(5)O(2), the tetra-zole ring and carboxyl group form a dihedral angle of 82.25 (14)°. In the crystal, adjacent mol-ecules are linked through O-H⋯N, N-H⋯O and N-H⋯N hydrogen bonds into layers parallel to the bc plane.

Related literature

For background to tetra­zole compounds, see: Zhao et al. (2008 ▶). For the use of 5-amino­tetra­zole-1-acetic acid in coord­ination chemistry, see: Li et al. (2010 ▶); Shen et al. (2011 ▶); Yang et al. (2008 ▶). For the crystal structures of similar compounds, see: Bryden (1956 ▶); Klapötke et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C3H5N5O2

M = 143.12

Monoclinic,

a = 18.381 (4) Å

b = 4.4429 (9) Å

c = 14.846 (3) Å

β = 90.850 (3)°

V = 1212.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.28 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.970, T max = 0.980

3040 measured reflections

1193 independent reflections

890 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.03

1193 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014389/cv5277sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014389/cv5277Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014389/cv5277Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C3H5N5O2	F(000) = 592
Mr = 143.12	Dx = 1.568 Mg m−3Dm = 1.568 Mg m−3Dm measured by not measured
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 734 reflections
a = 18.381 (4) Å	θ = 3.5–22.2°
b = 4.4429 (9) Å	µ = 0.13 mm−1
c = 14.846 (3) Å	T = 296 K
β = 90.850 (3)°	Block, colourless
V = 1212.2 (4) Å3	0.28 × 0.19 × 0.15 mm
Z = 8

Bruker APEXII CCD diffractometer	1193 independent reflections
Radiation source: fine-focus sealed tube	890 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −22→22
Tmin = 0.970, Tmax = 0.980	k = −5→4
3040 measured reflections	l = −13→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0657P)2 + 0.3572P] where P = (Fo2 + 2Fc2)/3
1193 reflections	(Δ/σ)max = 0.002
92 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O2	0.17856 (8)	0.1746 (3)	0.30324 (8)	0.0527 (4)
H2	0.1626	0.2644	0.3470	0.079*
N2	0.18104 (10)	0.4658 (4)	0.01590 (11)	0.0493 (5)
N3	0.15090 (8)	0.2586 (4)	0.06465 (10)	0.0414 (4)
C3	0.14844 (11)	0.2824 (5)	0.22938 (12)	0.0426 (5)
N4	0.08911 (9)	0.1468 (4)	0.03036 (11)	0.0485 (5)
N1	0.13778 (10)	0.4994 (4)	−0.05556 (11)	0.0500 (5)
C2	0.18346 (11)	0.1507 (5)	0.14771 (12)	0.0449 (5)
H2A	0.2348	0.2010	0.1487	0.054*
H2B	0.1793	−0.0668	0.1499	0.054*
O1	0.10122 (10)	0.4680 (4)	0.22631 (10)	0.0752 (6)
C1	0.08229 (11)	0.3035 (5)	−0.04569 (13)	0.0479 (5)
N5	0.02757 (11)	0.2722 (6)	−0.10567 (13)	0.0787 (8)
H5A	−0.0064	0.1434	−0.0962	0.094*
H5B	0.0264	0.3809	−0.1536	0.094*

	U11	U22	U33	U12	U13	U23
O2	0.0661 (10)	0.0609 (10)	0.0308 (8)	0.0097 (8)	−0.0064 (6)	−0.0009 (6)
N2	0.0611 (10)	0.0547 (11)	0.0320 (9)	−0.0062 (9)	−0.0015 (7)	0.0015 (7)
N3	0.0464 (9)	0.0479 (10)	0.0300 (8)	0.0011 (7)	0.0009 (7)	−0.0019 (7)
C3	0.0479 (11)	0.0467 (12)	0.0329 (10)	0.0005 (10)	−0.0036 (8)	−0.0002 (8)
N4	0.0490 (9)	0.0622 (11)	0.0341 (9)	−0.0039 (8)	−0.0029 (7)	0.0042 (8)
N1	0.0604 (11)	0.0588 (12)	0.0309 (9)	−0.0029 (9)	−0.0027 (7)	0.0027 (7)
C2	0.0506 (11)	0.0502 (12)	0.0337 (10)	0.0068 (10)	−0.0047 (8)	0.0013 (8)
O1	0.0878 (12)	0.0979 (14)	0.0398 (9)	0.0459 (11)	−0.0038 (8)	−0.0048 (8)
C1	0.0483 (11)	0.0651 (14)	0.0303 (10)	0.0030 (10)	0.0015 (8)	0.0015 (9)
N5	0.0607 (12)	0.125 (2)	0.0503 (12)	−0.0216 (12)	−0.0165 (9)	0.0320 (12)

O2—C3	1.312 (2)	N4—C1	1.331 (3)
O2—H2	0.8200	N1—C1	1.351 (3)
N2—N3	1.300 (2)	C2—H2A	0.9700
N2—N1	1.325 (2)	C2—H2B	0.9700
N3—N4	1.334 (2)	C1—N5	1.341 (2)
N3—C2	1.444 (2)	N5—H5A	0.8600
C3—O1	1.198 (2)	N5—H5B	0.8600
C3—C2	1.500 (3)
C3—O2—H2	109.5	N3—C2—H2A	109.1
N3—N2—N1	105.66 (16)	C3—C2—H2A	109.1
N2—N3—N4	114.75 (16)	N3—C2—H2B	109.1
N2—N3—C2	122.39 (16)	C3—C2—H2B	109.1
N4—N3—C2	122.81 (17)	H2A—C2—H2B	107.8
O1—C3—O2	125.45 (18)	N4—C1—N5	124.7 (2)
O1—C3—C2	123.87 (18)	N4—C1—N1	111.56 (17)
O2—C3—C2	110.64 (17)	N5—C1—N1	123.72 (19)
C1—N4—N3	101.42 (17)	C1—N5—H5A	120.0
N2—N1—C1	106.60 (16)	C1—N5—H5B	120.0
N3—C2—C3	112.53 (16)	H5A—N5—H5B	120.0
N1—N2—N3—N4	0.2 (2)	O1—C3—C2—N3	−3.6 (3)
N1—N2—N3—C2	177.93 (17)	O2—C3—C2—N3	178.80 (17)
N2—N3—N4—C1	−0.1 (2)	N3—N4—C1—N5	179.7 (2)
C2—N3—N4—C1	−177.82 (17)	N3—N4—C1—N1	0.0 (2)
N3—N2—N1—C1	−0.2 (2)	N2—N1—C1—N4	0.2 (2)
N2—N3—C2—C3	101.8 (2)	N2—N1—C1—N5	−179.6 (2)
N4—N3—C2—C3	−80.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O1i	0.86	2.36	3.080 (3)	141
N5—H5A···N4ii	0.86	2.23	3.064 (3)	163
O2—H2···N1iii	0.82	1.85	2.665 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5B⋯O1i	0.86	2.36	3.080 (3)	141
N5—H5A⋯N4ii	0.86	2.23	3.064 (3)	163
O2—H2⋯N1iii	0.82	1.85	2.665 (2)	172

Symmetry codes: (i) ; (ii) ; (iii) .